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#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/76/2007658.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2007658
loop_
_publ_author_name
' Hajime Irikawa '
' Kinya Iijima '
_publ_section_title
;
 2,6-Dimethyl-3,7-diphenyl-2,6-naphthyridine-1,5(2H,6H)-dione
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1318
_journal_page_last               1320
_journal_paper_doi               10.1107/S0108270198003333
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C22 H18 O2 N2'
_chemical_formula_sum            'C22 H18 N2 O2'
_chemical_formula_weight         342.4
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source           'International Tables (1974)'
_cell_angle_alpha                90.00000
_cell_angle_beta                 93.94(2)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            4
_cell_length_a                   23.138(5)
_cell_length_b                   11.220(2)
_cell_length_c                   6.8820(10)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.3
_cell_measurement_theta_min      4.5
_cell_volume                     1782.4(6)
_computing_cell_refinement       'MXC diffractometer system (MAC Science, 1989)'
_computing_data_collection       'MXC diffractometer system (MAC Science, 1989)'
_computing_data_reduction        'Crystan (Gilmore & Brown, 1988)'
_computing_molecular_graphics    'ORTEP (Johnson, 1965) in Crystan'
_computing_publication_material  Crystan
_computing_structure_refinement  Crystan
_computing_structure_solution    Crystan
_diffrn_measurement_device       'MAC Science MXC3'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_type           'Mo K~\a~'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4646
_diffrn_reflns_theta_max         26.43
_diffrn_standards_decay_%        ' < 1 '
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      1.26
_exptl_crystal_density_method    ' floatation in KI aqueous solution'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2515
_refine_ls_R_factor_gt           0.0669
_refine_ls_shift/su_max          0.0003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0004F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0694
_reflns_number_gt                1598
_reflns_number_total             4081
_reflns_threshold_expression     ' I > 2.0 σ(I)'
_cod_data_source_file            oa1045.cif
_cod_data_source_block           oa1045
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C22 H18 O2 N2'
_cod_database_code               2007658
_cod_database_fobs_code          2007658
loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-Z
-X+0.5,+Y+0.5,-Z+0.5
+X+0.5,-Y+0.5,+Z+0.5
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_type_symbol
C1 -.0581(2) .1198(4) .4724(7) .043(3) Uani C
N1 -.02208(17) .2162(3) .4428(5) .043(2) Uani N
C2 .0377(2) .2046(4) .4311(7) .042(3) Uani C
C3 .0631(2) .0967(4) .4581(7) .040(3) Uani C
C4 .02951(18) -.0049(4) .4977(6) .037(3) Uani C
O1 -.11111(14) .1333(3) .4754(5) .055(2) Uani O
C5 -.0508(2) .3343(5) .4391(9) .068(4) Uani C
C6 .0728(2) .3105(4) .3819(7) .047(3) Uani C
C7 .0596(2) .3791(5) .2173(8) .056(3) Uani C
C8 .0970(3) .4694(5) .1696(9) .072(4) Uani C
C9 .1465(3) .4918(6) .2828(12) .086(5) Uani C
C10 .1600(3) .4250(6) .4453(11) .082(5) Uani C
C11 .1232(3) .3348(5) .4960(8) .064(4) Uani C
C21 .0499(2) -.1343(4) .0413(6) .039(3) Uani C
N2 .10188(15) -.0753(4) .0200(5) .040(2) Uani N
C22 .1055(2) .0445(4) -.0302(6) .040(3) Uani C
C23 .0569(2) .1113(4) -.05000(7) .040(3) Uani C
C24 .0024(2) .0600(4) -.0208(6) .036(3) Uani C
O2 .04881(14) -.2418(3) .0755(5) .054(2) Uani O
C25 .1543(2) -.1478(5) .0649(8) .063(4) Uani C
C26 .1632(2) .0965(4) -.0659(7) .042(3) Uani C
C27 .1833(2) .1920(5) .0479(8) .064(4) Uani C
C28 .2353(3) .2475(6) .0111(10) .077(4) Uani C
C29 .2663(2) .2080(6) -.1369(10) .076(4) Uani C
C30 .2462(2) .1163(5) -.2520(9) .062(4) Uani C
C31 .1949(2) .0592(5) -.2156(7) .050(3) Uani C
H25A .19044 -.10758 .05086 .060 Uiso H
H25B .15264 -.21568 -.02034 .060 Uiso H
H25C .15384 -.17488 .19726 .060 Uiso H
H31 .18184 -.00706 -.29542 .060 Uiso H
H30 .26764 .09104 -.35941 .060 Uiso H
H29 .30263 .24509 -.16033 .060 Uiso H
H28 .24910 .31318 .09076 .060 Uiso H
H27 .16116 .22038 .15159 .060 Uiso H
H23 .05946 .19423 -.08325 .060 Uiso H
H5A -.02588 .40077 .41854 .060 Uiso H
H5B -.06718 .34507 .56244 .060 Uiso H
H5C -.08138 .33437 .33734 .060 Uiso H
H7 .02490 .36414 .13668 .060 Uiso H
H8 .08787 .51672 .05524 .060 Uiso H
H9 .17199 .55453 .24771 .060 Uiso H
H10 .19483 .44139 .52495 .060 Uiso H
H11 .13313 .28798 .61054 .060 Uiso H
H3 .10420 .08923 .45089 .060 Uiso H
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C4 . 2_556 116.0(5) yes
N1 C1 O1 . . 120.8(5) yes
C4 C1 O1 2_556 . 123.1(5) yes
C1 N1 C2 . . 122.8(4) yes
C1 N1 C5 . . 115.2(4) yes
C2 N1 C5 . . 121.8(4) yes
N1 C2 C3 . . 119.9(5) yes
N1 C2 C6 . . 119.7(5) yes
C3 C2 C6 . . 120.4(5) yes
C2 C3 C4 . . 120.5(5) yes
C1 C4 C3 2_556 . 119.3(4) yes
C1 C4 C4 2_556 2_556 120.7(5) yes
C3 C4 C4 . 2_556 120.0(5) yes
C2 C6 C7 . . 122.4(5) yes
C2 C6 C11 . . 118.5(5) yes
C7 C6 C11 . . 118.8(5) yes
C6 C7 C8 . . 119.6(6) yes
C7 C8 C9 . . 120.9(6) yes
C8 C9 C10 . . 120.2(7) yes
C9 C10 C11 . . 119.9(7) yes
C6 C11 C10 . . 120.6(6) yes
N2 C21 C24 . 2_555 115.7(5) yes
N2 C21 O2 . . 121.2(5) yes
C24 C21 O2 2_555 . 123.2(5) yes
C21 N2 C22 . . 123.6(4) yes
C21 N2 C25 . . 114.9(4) yes
C22 N2 C25 . . 121.4(4) yes
N2 C22 C23 . . 119.8(5) yes
N2 C22 C26 . . 119.2(4) yes
C23 C22 C26 . . 121.0(5) yes
C22 C23 C24 . . 120.3(5) yes
C21 C24 C23 2_555 . 119.5(4) yes
C21 C24 C24 2_555 2_555 119.6(5) yes
C23 C24 C24 . 2_555 120.8(5) yes
C22 C26 C27 . . 118.5(5) yes
C22 C26 C31 . . 122.4(5) yes
C27 C26 C31 . . 119.0(5) yes
C26 C27 C28 . . 120.1(6) yes
C27 C28 C29 . . 119.8(6) yes
C28 C29 C30 . . 120.4(6) yes
C29 C30 C31 . . 120.4(6) yes
C26 C31 C30 . . 120.3(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . . 1.389(7) yes
C1 C4 . 2_556 1.457(7) yes
C1 O1 . . 1.238(6) yes
N1 C2 . . 1.397(7) yes
N1 C5 . . 1.481(7) yes
C2 C3 . . 1.353(7) yes
C2 C6 . . 1.491(7) yes
C3 C4 . . 1.417(7) yes
C4 C4 . 2_556 1.373(6) yes
C6 C7 . . 1.387(8) yes
C6 C11 . . 1.389(8) yes
C7 C8 . . 1.386(9) yes
C8 C9 . . 1.364(10) yes
C9 C10 . . 1.365(11) yes
C10 C11 . . 1.383(9) yes
C21 N2 . . 1.389(6) yes
C21 C24 . 2_555 1.469(7) yes
C21 O2 . . 1.230(6) yes
N2 C22 . . 1.391(7) yes
N2 C25 . . 1.476(7) yes
C22 C23 . . 1.351(7) yes
C22 C26 . . 1.493(7) yes
C23 C24 . . 1.412(7) yes
C24 C24 . 2_555 1.383(7) yes
C26 C27 . . 1.388(8) yes
C26 C31 . . 1.371(7) yes
C27 C28 . . 1.394(9) yes
C28 C29 . . 1.360(10) yes
C29 C30 . . 1.360(10) yes
C30 C31 . . 1.387(8) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139056191
